Carbon tetrabromide → 2-(4-(2-bromoethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-one

HRID 591768ノート

反応式

HRID 591768 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:24])[NH:5][C:6]([C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([O:19][CH2:20][CH2:21]O)=[C:14]([CH3:23])[CH:13]=1)=[N:7]2.C(Br)(Br)(Br)[Br:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C>[Br:26][CH2:21][CH2:20][O:19][C:15]1[C:16]([CH3:18])=[CH:17][C:12]([C:6]2[NH:5][C:4](=[O:24])[C:3]3[C:8](=[CH:9][CH:10]=[CH:11][C:2]=3[Cl:1])[N:7]=2)=[CH:13][C:14]=1[CH3:23]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1361833855-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one

生成物 1

HCID 1364150762-(4-(2-bromoethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-one収率 88.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one (0.40 g, 1.16 mmol) in anhydrous DMF (10 mL) was added carbon tetrabromide (0.42 g, 1.27 mmol) and triphenylphosphine (0.33 g, 1.27 mmol). The reaction mixture was stirred at room temperature for 27 hours. Solvent was evaporated to dryness in vacuo and the residue triturated with Et2O (15 mL)/EtOAc (15 mL) to give 2-(4-(2-bromoethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-one (0.42 g). It was used without further purification. The 1H NMR indicated a purity of about 45%.

後処理

  1. customSolvent was evaporated to dryness in vacuo
  2. customthe residue triturated with Et2O (15 mL)/EtOAc (15 mL)

出典と根拠

ORDレコード
ord-ea6f020bd720458293f4903fe42d477f
出典データセット
uspto-grants-2016_01
特許番号
US09238640B2

反応ノート

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